o-allylphenyl cyclohexyl ether

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-allylphenyl cyclohexyl ether
• 英文别名: 1-Cyclohexyloxy-2-prop-2-enylbenzene
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: TWXBVKKYUCICKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氯代环己烷 、 2-烯丙基酚 在 silver nitrate 作用下， 反应 4.0h， 以6%的产率得到o-allylphenyl cyclohexyl ether
  参考文献：
  名称：

  Photochemistry of o-allylphenol. Identification of the minor products and new mechanistic proposals

  摘要：

  The photochemistry of o-allylphenol (1) in cyclohexane has been reinvestigated. Besides the previously reported cyclic ethers 2 and 3, seven additional minor photoproducts have been detected. Spectroscopic methods, coupled with independent synthesis, have allowed their identification as 2-methylbenzofuran (5), o-propylphenol (8), the epoxide 4, the dihydroxy compound 9, the cyclohexyl ether 6, o-(cyclohexylmethyl)phenol (10), and the dimer 7. Their formation is rationalized through new mechanistic pathways, which involve initial intermolecular electron and/or proton transfer between two molecules of o-allylphenol, as well as di-pi-methane rearrangement. Key intermediates appear to be radical V, carbenium ion IX, and carbene XI. This is supported by photolysis of o-allylphenyl acetate (I 1), which leads to the formation of a radical pair, followed by in cage recombination to the photo-Fries products 12 and 13 or, alternatively, diffusion of the radicals out of the solvent cage to afford the minor products 2, 5, and 6, identical to those obtained by photolysis of 1.

  DOI：

  10.1021/jo00064a016

文献信息

• Miranda Miguel A., Tormos Rosa, J. Org. Chem., 58 (1993) N 12, S 3304-3307
  作者：Miranda Miguel A., Tormos Rosa

  DOI：——

  日期：——